For a half-century, Donald Trump has portrayed himself as the consummate dealmaker — and the ultimate escape artist, a serial entrepreneur turned politician who managed to avoid major consequences despite having been investigated in every decade of his adult life by federal and state agencies, by bankers and casino regulators, by legions of prosecutors and competitors.
He’s been investigated over matters small and huge: over alleged lobbying violations in New York state and whether he played a role in the Russian government’s effort to interfere with the 2016 U.S. presidential election. He was the only president to be impeached twice, yet he was acquitted both times.
Now, 50 years after federal officials first accused Trump and his father of violating laws that barred racial discrimination in apartment rentals, the former president has been indicted, according to multiple people briefed on the matter. While the indictment has not been made public, a Manhattan grand jury has been investigating the payment of hush money to a professional stripper and adult film actress who threatened to go public with her allegation that Trump had an affair with her years before he won the White House.
The indictment of the former president is likely to spark a political firestorm and might break new ground legally. It is also a moment that Trump has long believed could never happen — a criminal charge that could theoretically put him behind bars after a career of dodging findings of guilt in forums from Trenton, N.J., to Brooklyn to the U.S. Capitol.
“Donald was always fearless,” said Barbara Res, an engineer and attorney who was a top executive at the Trump Organization for two decades. “He absolutely believed he was above the law. He loved cutting corners. He loved suing people.’”
To Trump, an indictment is a first step in a very public drama that he believes will ultimately accrue to his benefit, according to people who have worked closely with him through the years, bolstering his support among his base and winning sympathy from other voters who might not like him but also don’t believe that a former president should be prosecuted in a case stemming from an alleged extramarital affair.
Trump, now in his third consecutive presidential campaign, will win in 2024 because of the Stormy Daniels case, said his new lawyer Joe Tacopina, speaking on MSNBC: “I believe this will catapult him into the White House. … Because this will show how they are weaponizing the justice system. They’re taking the vote out of the voters’ hands.”
The indictment in the Daniels case comes amid an Atlanta-area investigation into Trump’s role in seeking to overturn the 2020 election results in Georgia, and a special counsel’s federal investigations into Trump’s actions leading up to the Jan. 6, 2021, riot at the Capitol, as well as his handling of classified documents at Mar-a-Lago, his South Florida estate and private club.
Already, Trump’s statements about the Daniels case have followed a pattern he set as far back as 1973, when federal prosecutors accused Trump and his father, Fred, a prominent New York City apartment developer, of turning away Black people who wanted to rent from them. In that case, Trump first denied the allegation, then said he didn’t know his actions were illegal, and then, through his lawyer, accused the government of conducting a bogus “Gestapo-like investigation.”
This time, Trump initially said he’d never had any sexual relationship with Daniels or that, as he told friends privately, Daniels was not his type. Then, he said he didn’t know Daniels had been paid $130,000 to remain silent about their alleged relationship, which he denies existed. And then he said that perhaps he had known about the payment, but that he never ordered his attorney, Michael Cohen, to make it.
Finally, Trump spokesman Steven Cheung said in a statement Thursday evening that “From Russia, Russia, Russia, to the Mueller Hoax, to Impeachment Hoaxes 1 and 2, and even the Unlawful Mar-a-Lago Raid, Democrats have investigated and attacked President Trump since before he was elected — and they’ve failed every time. Now Democrats are at it again, pushing the ‘Nuclear Button’ and attacking a president because of a disgraced extortionist.”
Trump’s attitude toward law, lawyers and the notion of legal jeopardy closely tracks his approach to business, politics and personal relationships: He has said that he believes in instinct and gut over expertise and rules, that any publicity is good publicity, and that most Americans admire successful people even when — or especially when — they skirt the rules.
Just as he improvised his way through episodes of “The Apprentice,” the NBC reality show that ran from 2004 to 2017 and jump-started his pivot into politics, Trump has said he prefers to wing it when it comes to sitting for depositions or appearing as a witness. Longtime aides say he has always believed investigations into his business practices or personal life were politically motivated and that he could persuade any jury that he’s been singled out for unfair attack.
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Whether the forum is a television show, a courtroom or a political debate, Trump contends he can outperform any adversary. “I’ve never had lessons,” Trump said in a 2015 interview with The Washington Post about why he doesn’t rehearse for debates. “Either you’re good at it or you’re not good at it.”
Trump’s confidence that he can finesse legal proceedings stems from two sources: his father, who cultivated close ties with Democratic Party officials and well-connected lawyers, and New York power broker Roy Cohn, a lawyer — later disbarred for fraud and misrepresentation — who taught the young Donald how to turn tables on prosecutors.
In 1973, when Trump met Cohn at Le Club, a members-only New York nightspot, the 27-year-old and his father were under investigation by the Justice Department for discriminating against Black New Yorkers in renting apartments. Donald was just starting his own business, seeking to build in Manhattan, which he saw as a major step up from his father’s base in Brooklyn and Queens. Trump had been rejected by Le Club, but finally won admission when he promised not to hit on married women there, as Trump recounted in his book, “Trump: The Art of the Deal.”
At their first meeting, he told Cohn: “I don’t like lawyers. … They are always looking to settle instead of fight.”
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Cohn agreed and advised Trump to tell the feds “to go to hell and fight the thing in court.” Cohn spelled out a strategy Trump would use for the rest of his career: When attacked, counterattack with overwhelming force.
On behalf of Trump, Cohn filed a $100 million counterclaim against the government. In a deposition, Trump toyed with prosecutors, contending that he was “unfamiliar” with housing discrimination law.
His counterclaim was tossed out of court, but Cohn and Trump managed to stretch the proceedings over two years, finally agreeing to a settlement in which Trump admitted no wrongdoing. In the meantime, he won a load of free publicity — negative stories “can be very valuable to your business,” he said back then — and established himself as a fighter.
Over the next half-century, Trump would push back in similar ways against casino regulators who alleged his business empire had become financially unstable, against New York state’s effort to shut down his Trump University for defrauding students, and against Congress as it twice impeached — and acquitted — the 45th president for “high crimes and misdemeanors.”
In the Daniels case, Trump has deployed almost the identical playbook he learned from Cohn, starting with his blanket denial that he had an affair with the adult-movie star after they met at a celebrity golf tournament in Lake Tahoe, Nev., in 2006, when she was 27 and he was 60.
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Trump has a long history of marketing himself as a billionaire playboy with a knack for dating top models. Before, between and during his three marriages, he arranged to be photographed with beauty pageant winners and models in skimpy outfits, visited Hugh Hefner’s Playboy mansion, bought and managed beauty contests, and ended up in legal battles with women who said he had groped them or had affairs with them.
Those disputes generally ended in settlements, with the women involved receiving a payment and agreeing to sign a nondisclosure pact. Daniels, whose real name is Stephanie Clifford, revealed in 2018 that Cohen, Trump’s attorney, Cohen, had paid her $130,000 in the final weeks of the 2016 campaign to remain silent about an alleged sexual relationship with Trump.
Trump later admitted that he personally reimbursed Cohen for the hush money payments “to stop the false and extortionist accusations made by her about an affair.”
Although the politics of sexual abuse cases have changed markedly in recent years, Trump’s alleged improprieties have had little apparent impact on his popularity, a phenomenon that sets him apart from political and entertainment figures such as comedian Bill Cosby, Hollywood producer Harvey Weinstein, TV talk-show host Charlie Rose or U.S. Senate candidate Roy Moore of Alabama. This could be because voters long ago factored Trump’s personal behavior into their opinion about him as a candidate, or because he has persuaded die-hard supporters that he truly is a victim of “fake news.”
Popular attitudes toward politicians’ sexual misbehaviors tend to break along partisan lines. A quarter-century ago, many Democrats argued that President Bill Clinton’s affair with a White House intern was a private matter, while many Republicans viewed it as an example of public corruption. Similarly, in recent years, many Democrats have seized on allegations against Trump as proof that he was unfit for office, while many Republicans embraced his denials and said his policy achievements were more important than any personal misdeeds.
The public’s perception of cases like this can flip virtually overnight depending on which party the accused belongs to. When the Deseret News in Salt Lake City conducted a national poll about adultery at the beginning of the 2016 campaign, almost two-thirds of Democrats said an extramarital affair wouldn’t affect their voting decision, while just under half of Republicans agreed that an affair wouldn’t matter.
One year later, when the same poll posed the same question in a country where Trump was president, the results were upended: Then 57 percent of Republicans were willing to look past an affair, while 47 percent of Democrats were ready to ignore a candidate’s indiscretions.
The Daniels case, meanwhile, centers not on whether Trump had an affair but on the hush money and whether it was an illegal campaign contribution.
Why that question, rather than Trump’s actions leading up to the Jan. 6, 2021, attack on the Capitol or his efforts to overturn the Georgia election results, has led to the first indictment of a former president is more a matter of the vagaries of different prosecutors’ approaches to their cases than any reflection of the relative importance or validity of the accusations.
Manhattan District Attorney Alvin Bragg has said his decision to press charges would be based on his investigators’ confidence in their ability to prove the case. His prosecutors “are going through documents, interviewing witnesses, and exploring evidence not previously explored,” Bragg told The Post last year. “In the long and proud tradition of white-collar prosecutions at the Manhattan D.A.’s Office, we are investigating thoroughly and following the facts without fear or favor.”
Those who have worked closely with Trump through past legal troubles say that despite his public bravado, he sometimes privately shows genuine concern that he could end up financially ruined or behind bars.
“Oh, my God, this is terrible,” Trump said after learning that former FBI chief Robert S. Mueller III would be the special counsel in the federal investigation of Russia’s effort to interfere in the 2016 election, according to Mueller’s final report. “This is the end of my presidency. … I’m f—ed.”
Similarly, when representatives of 30 banks confronted Trump in 1990, when he owed $3.2 billion and the bankers put liens on his house, boat and Florida mansion, “he was scared,” Res said. “He stopped bragging so much. He was subdued. It was a visceral thing and we all saw it.”
But more than three decades later, much as she would like to see Trump held accountable, Res has come to believe that he will outmaneuver prosecutors who come after him.
“I don’t think they’ll get him,” she said. “Just like Mueller backed off, they won’t have the courage to go after him all the way. But oh, that would be so great.”